Exchange Server 2010: Multiple Domains + Multiple Send As Addresses + PC + Mac + iPhone

I have recently installed a new Exchange 2010 Server for a company in Los Angeles.  They have an office with about 30 users and all of these users use the Exchange server for their company email on one domain (let’s call it  However, a partial owner of the company who works offsite has two additional email domains he requires mail services for (let’s call this and  This partial owner has email addresses in all three domains, and needs to be able to send mail from each of these addresses on all of his devices.  This user uses a PC running Outlook 2010, a Mac running Office 2011 for Mac, and an iPhone.

The Exchange server has been setup to accept mail from all three domains correctly.  Due to Exchange’s limitations on sending from alias addresses, I have setup three AD users for the partial owner with three separate Exchange mailboxes.  Originally, I setup all three Exchange accounts in Outlook 2010 on his PC to connect to the Exchange server using Outlook Anywhere (RPC over HTTP).  However, this setup does not meet his requirements as it creates three separate mailboxes, three contact lists, and three calendars in his Outlook profile.  He wants one calendar, one contact list, and one mailbox that both accepts and sends mail from all three accounts.  He also requires that these sync across all of his devices.

For the PC running Outlook 2010, this is relatively easy to do.  I can forward mail from the and to his account.  I can then give him “Send As” permissions on the and accounts on the Exchange server, then instruct him to use the “From” field in Outlook to select the appropriate email address when sending mail.  Unfortunately, he needs this same sending capability on his Mac and iPhone.  I know the iPhone connects to Exchange using ActiveSync, but somehow I doubt ActiveSync will properly communicate the “Send As” permissions on the and accounts with the configured Exchange account.

I was thinking that perhaps a solution would be to enable POP on the new Exchange server, setup the iPhone with the Exchange account as well as a POP account for and accounts.  Since mail sent to his and accounts are being forwarded to the mailbox, he should not receive duplicate mail with these POP accounts configured on his phone, and it would allow him to send from all three addresses.  With this configuration, however, I doubt mail sent from his iPhone would appear in his Exchange sent items folder.

I could really use some help with this.  I spent the better part of the last five days (including my weekend) doing their server migrations and taking care of the 30 users in his office.  This included a new domain controller, a new exchange server deployment, a new SQL server deployment, a new terminal services deployment, and migrations of everything from their old servers.  Now that the office is squared away, my reward is a frustrated owner who works off-site and has special email needs that are cross-platform.

I’m really spent and could use help from my fellows in the trenches.  Thanks guys.
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Aaron TomoskyConnect With a Mentor SD-WAN SimplifiedCommented:
If you don't mind IMAP, the iPhone can do multiple send as with a hidden trick

Then use the exchange connection for just contacts and calendar.
Interesting one, the following eludes that your on the right path but check out the last entry,

"Haven't tried this in Exchange 2010 but this is a workaround we use in Exchange 2007 for a small handful of users needing to occasionally send from another email address, but they want all replies coming into a single mailbox.

Remove the secondary SMTP address from the user's Exchange mailbox and assign it to a newly created mail enabled Universal Security group that has been given a similar name as the mailbox.  Add the user mailbox account to the security group as the only member.  Permission the security group to give the user mailbox account Send As permissions.

This will allow emails sent to both SMTP addresses to route to the user mailbox while allowing the user to reply to emails from either the primary SMTP of their mailbox, or they can change the From address in Outlook on that email to the SMTP address of the security group so the emails send out from the other address.  The good thing is that it works well.  The bad thing is that they need to remember to change the From address every time they need to send from the SMTP assigned to the security group.  Not super user friendly but better than nothing."

this should work but on a mobile device? not sure about that.
jHillymanAuthor Commented:
Thank you very much!
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